Chloroacetone → HCID 20222894, compound

HRID 979944Notes

Reaction equation

HRID 979944 reaction equation
[Cl:1][CH2:2][C:3](=[O:5])[CH3:4].[O:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[CH2:11][N:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[C:13]1[NH:21][CH:22]1[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][NH:30][C:31]([NH2:33])=[S:32])[CH2:24][CH2:23]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C(=O)C>O>[OH2:5].[ClH:1].[ClH:1].[ClH:1].[O:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[CH2:11][N:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[C:13]1[NH:21][CH:22]1[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][NH:30][C:31]2[S:32][CH:2]=[C:3]([CH3:4])[N:33]=2)[CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 13769778HCID 13769778, compound

Product 1

HCID 20222894HCID 20222894, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.3 parts of 1-chloro-2-propanone, 5 parts of N-[2-[4-[[1-(2-furanylmethyl)-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]thiourea, 3 parts of potassium carbonate and 68 parts of N,N-dimethylacetamide was stirred overnight at room temperature. Water was added and the product was extracted with 4-methyl-2-pentanone. The extract was dried, filtered and evaporated. The oily residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the hydrochloride salt in 2-propanol. The salt was filtered off and dried overnight in vacuo at 100° C., yielding 3.8 parts of 1-(2-furanylmethyl)-N-[1-[2-[(4-methyl-2-thiazolyl)amino]ethyl]-4-piperidinyl]-1H-benzimidazol-2-amine trihydrochloride monohydrate; mp. 238.5° C. (compound 88).

Workup

  1. extractionthe product was extracted with 4-methyl-2-pentanone
  2. customThe extract was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe oily residue was purified by column chromatography over silica gel using
  6. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated
  9. filtrationThe salt was filtered off
  10. customdried overnight in vacuo at 100° C.

Sources & evidence

ORD record
ord-f3643f43eed8460d97b7e7f2ea0634a6
Source dataset
uspto-grants-1987_01
Patent number
US04634704

Reaction notes

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